Top 30 Questions to Ask Software Developers

Ever wonder why software development projects can feel challenging? It is frequently down to a lack of understanding between clients and developers about the project specifics and vision.

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Software project management is no picnic. It doesn’t matter if you are an established enterprise with thousands of clients or a fresh startup in your industry. Understanding the important questions to ask software developers can be a bamboozling task when attempting a digital transformation. However, it is vital, as without effective communication and understanding between you and the software developer, you may end up choosing an unsuitable candidate for your project or you may be left feeling confused or dissatisfied with the results at the end.

It is also crucial to ask the right questions in the right subject area to allow the software developer or consultant to generate a proposal that is as close as possible to your vision. Subsequently, the greater the information and understanding between you, the more precise the proposal which will save time, money, and sleepless, tedious nights on both ends.

As world-beating software developers ourselves, we appreciate that the right questions to ask may not always be that obvious. So we have devised what we consider the most important questions to ask a software developer when undertaking digital transformations at your organization. The questions we have come up with are centered around the concepts of agile management, communication, billing, processes, team, and relevant experience before delving into what red flags you should look out for and what traits you should avoid in a software developer.


Firstly, we will review questions regarding project management, specifically agile management. These questions revolve around the company’s project operations, ranging from time effectiveness and adaptability to transparency.

This is important to cover as it will allow the client to understand how they will be able to keep up to date and track the timeline of your app or website development project.

Project management methods can vary greatly between developers so it is important to determine who best fits your project vision and ask the following questions:

  • How do you estimate project timelines?
  • What’s the first step you take in a project?
  • What’s your project management style?
  • What happens if things change?
  • How close to your estimated number of hours do you typically come to (margin of 5%? 10%? 20%?)
  • How do you estimate the length of this project?
  • What are the strategic goals of the application for your business?


Ensuring effective communication between you and the developer in a software project is pivotal in creating a better, mutually beneficial relationship.

By clarifying deadlines, important dates, and how you intend to communicate, both parties can get on the same page and nobody is left in the dark regarding the important aspects of the project. Effective communication can also improve the trust between you and the developer. Thus, when difficult situations arise they can be resolved much quicker.

Additionally, how the developer responds to these questions will provide plenty of insight into whether they are a good fit for your project or not.

  • What is the potential for updates?
  • How will you ensure that you understand my project’s requirements?
  • How and when will you communicate with me?
  • What files will the client have access to during the project?
  • What are the critical dates for the product?


When it comes to software development projects, it is important to work out a realistic budget, and find a development agency that can work within that budget. Discussing the developer’s pricing options and the estimated cost of your project will allow you to get a sense of whether or not the agency is a good fit.

Ensuring that both parties understand the financial demands early on in the process will also eliminate any confusion or awkward conversations you may have towards the end of the project.

Although it may be challenging to estimate the exact cost right away, a website or app development agency should be able to give you a realistic price range after considering your proposal.

  • How much would it cost and what would the price include?
  • How do you bill? Is it a project package or is it an hourly payment?
  • Do you offer flexible pricing packages? (i.e. some agencies such as Cogify will accept part of the payment in shares and come up with creative ways to make the budget work for both parties)


Asking the right questions regarding the development process is essential as it is fundamentally the core of the project. This will provide a broader comprehension of how the project will be carried out, the processes involved in it, and whether these processes translate into a good fit for you.

Without gaining insights into the development process, you may end up feeling confused about what the developer is doing, the level of specialization the developer has for your project area, and what is expected of you throughout the process.

  • How are intellectual rights handled?
  • What is your software design and development process and why?
  • What involvement will be expected from me throughout the process?
  • What technologies do you specialise in?
  • What do you expect from the application at the end of the development process?

The team

Gaining an insight into the development team is another important aspect to consider when planning an app or website development project. Based on the requirements of your project, a software development company should be able to advise the roles and expertise needed to complete it.

Getting a better understanding of the way a development team operates allows you to gain insight into whether or not the company is best suited to your needs, has the relevant expertise for the project, and whether their ethos and people reflect your values.

Furthermore, knowing which team member plays what role in the development process means you know where to direct your questions depending on which aspect of the project it relates to.

  • Are contractors used for any of the work?
  • How many developers do you have?
  • How long will it take to scale up the team assigned to the project?
  • Will there be a specific person of contact?
  • Tell me about your company, as well as the specific team I’ll be working with.
  • Who is responsible for the approval of the design and tech approaches on the client’s side?


Understanding the prior experience of a software development company in tackling projects similar to yours helps to confirm if they are well suited to your project.

A developer may claim to have extensive experience and a proven track record. However, you should ask them for a portfolio of their previous work and references from previous clients which will provide you with a better idea of work they have done in the past and whether this translates well to your project area.

Gaining insight into the company’s past work and operating procedures can consolidate whether or not they are worth what could be extensive time and financial investment.

  • What’s the success of your previous projects? Could you show me some references from your previous clients?
  • Do you have experience working with clients in my industry? Tell me about your experience completing projects similar to mine.
  • What makes you my best choice?
  • What information or resources about the market do you have?

Red flags

Software development is an important investment. It is not something you want half-baked, so you want to make sure that the person who you are selecting to carry out your vision is genuinely interested, trustworthy, and capable.

To find someone who you can trust to take on your project, it is necessary to separate the wheat from the chaff early on so that you aren’t left deciding between candidates who don’t fit the bill.

So what are some red flags that can help you identify right away who isn’t going to be able to fulfil your website or app development goals?

  1. Missed calls and appointments: Sloppy and inconsistent communication is a clear indicator of bad habits, presenting a large barrier to an effective workflow that is likely to cause delays to your project.

  2. Lack of interest in your project: Someone that takes pride in their work and genuinely wants to see your project excel will ask engaging questions to ensure they understand your proposal and are interested enough to see it through to the end. Those who are ambivalent, lacking enthusiasm and knowledge in your project are the types you should avoid.

  3. Lack of a work portfolio: When evaluating the skills of a software developer, you need to be able to see that they have been on quality, functioning web or software development projects in the past. Otherwise, you could be left with expensive mistakes.

  4. The agency or the developer is disorganized: Inquire about the structure of the team that will be responsible for your project; a well-put-together team where everyone has defined roles and responsibilities is a sure sign of high efficiency and organisation. If they are poorly organised, it''s a potential sign that your project will suffer from errors and delays.

  5. **Fixed time and scope for the project: **Software development projects come with a high degree of uncertainty and estimations become less accurate the further you are from completion. As appealing as it may be to fix the time and scope of the project right away, estimations are usually wrong and you risk impacting the effectiveness of your transformation if the developer is too focused on getting the product out by a certain time and not by the quality of the project.

Effective understanding between parties is a key factor in a successful software development project. Without asking the right questions, it is difficult for you to get an idea about the developer’s ability to take on your project, and for the developer to have the vital specific information to make your undertaking a success.

The project management questions listed above should give you a great idea of questions to ask software developers before and during a digital transformation. This will ensure that your software development project matches your vision.

Why not cut out the middleman and see what we can do for your next software project, contact us at hello@cogify.io or on LinkedIn and Twitter (@cogifyag), or simply head over to our website and have a look at the range of digital services we offer to benefit your business.

Ensuring that your organisation and the software developer have aligned goals is also key for a successful transformation. That is why we are an agency that offers part of the payment Cogify shares. We believe that your success is our success and we are firmly committed to long-term success and long-term partners.

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